You’re about to start a serious, monogamous relationship. How much time do you invest into really getting to know them before you commit?
Jobs are serious, monogamous relationships, yet most of us take the plunge after only a handful of hours. You can always quit and find another one, but inertia is stronger than you think.
Let’s cover some high-signal questions to learn the truth before you commit years of your life. They kick off what I call the Question Domino Effect. When you ask high-signal questions, you come off as more interested in them, which in turn, makes you more interesting:
These questions can also help you re-evaluate whether to stay or leave for greener pastures. Let’s get started!
What are the top 3 challenges facing the business?
Every business has a hierarchy of needs. Where you sit in their hierarchy determines the upper bound of your value to them. It also predicts the impact you can make, which shapes the story you tell when you leave.
A reliable way to predict challenges is to understand the life stage of the product, from conception to old age. A big company usually has products that span the spectrum, creating completely different learning experiences.
Here are some examples:
- During conception, you’ll need to talk to customers a lot, go deep on the market, build quickly and embrace uncertainty. Mortality can’t be taken for granted
- During adolescence, you’ll need to diagnose bottlenecks, optimize every step of the experience, build processes, and recruit new talent
- During adulthood, you’ll need to know your way around a P&L, diagnose cost drivers, make processes more efficient, and manage armies of stakeholders
Want a chill job? Work on products whose stage you’re intimately familiar with, or find something starting in late adulthood.
Want to grow quickly? Work on products whose stage is adjacent to your past experience, where you can bootstrap learning faster.
What kinds of people who are successful elsewhere don’t do well here?
Every place has its quirks. By adding the qualifier “who are successful elsewhere”, you filter out BS answers to reveal what they uniquely care about. Get to answers they don't advertise.
It’s also valuable to investigate leadership churn in your department. If there’s been a revolving door, ask around to see what happened. It’s usually a sign of changing priorities, which means your work may never see the light of day.
What’s the ideal mix of skills (execution, management, entrepreneurialism) for this role?
Misaligned expectations lie at the heart of disillusionment.
If you prefer to work on new products, you’ll feel stifled when your #1 task is to execute an established roadmap. If you’re a seasoned people manager, you might feel deflated leading an under-resourced team where you have to play part-time IC.
The thrill of a job title fades quickly, but your tasks will always be there waiting to color your experience.
What sort of progression would you like to see for the person in this role?
There are only three outcomes:
- You outgrow your role
- Role outgrows you
- You and your role grow together
#3 is rare, but can happen if you both want the same things at the same time.
Above all, this question reveals how much the company cares about promoting from within. Useful follow-up: “Is there someone who’s experienced this sort of progression? Can I chat with them?”
Talking to people not on your hiring panel is an effective way to avoid biased, practiced answers.
How are promotions and raises determined?
Companies vote with their wallets. The best way to determine what they really value is understanding the factors that go into promotions/raises, and how often it happens. It’s not all about money. Promotions assign future influence!
Smaller companies may not have a process yet, but they should still be able to speak to how they’ve made decisions or plan to make decisions.
What’s something you built that you’re proud of? How did it go from from idea to launch?
There are two big tells:
- What they pick
- Details on the product development process
Their source of pride shows you what they genuinely care about — does it help customers, drive more growth, increase profitability?
Their description of the process tells you how the sausage is made. Who’s pitching? Who’s validating? Who’s green-lighting? Asking for timelines can also get you a sense of their operating pace.
How will the world be different if we’re successful? What will it take to get there?
Take a good look at their vision and ambition — is this a ride you want to be on? Can they paint the destination and create the itinerary?
When you ask this of everyone on the leadership team, you expose the level of shared language around the big picture, and how aligned people really are. Unexpected differences become the faultlines that make it difficult to get stuff done. How much narrative debt have they accrued?
How will this team be different if we’re successful?
People who come up with big ideas are often blind to what it means for the people that actually do the work. They’re more interested in things than people.
When I was in consulting, I noticed that teams on the sexiest projects tended to feel the most burned out and mistreated. This pattern holds for many companies. Those with glamorous visions are some of the toughest to work for — when you can attract top-tier talent without having a good culture, you don’t need good culture.
Sometimes the experience is worth the compromise, but you’ll always be happier when you go in with open eyes.
Unlike most relationships, a company’s unlikely to change for you, but the best ones change you for the better. When you sign an offer, you’re choosing to enter a world you don’t control, so it’s crucial to understand the rules and motivations of the creators.
Asking questions is also a positive sum game. Not only do you invite them to share their unfiltered self, you also get to show them how you approach a decision where you have major skin in the game — the decision of whether to join at all.
👋 P.S. Want to join a top startup? Check out who's newly funded and hiring or benchmark your startup salary & equity with hundreds of data points!